Casciaro came through the ranks of Lincoln Red Imps with brothers Ryan and Lee, becoming ever present in the dominant Red Imps team that won 6 of its 14 consecutive league titles from 2010 to 2016.

However, in January 2018 he came out of retirement, re-joining Lincoln while joining FC Olympique 13 on loan for the rest of the season, in order to regain match fitness.

[1] Casciaro made his international debut with Gibraltar on 19 November 2013 in a 0–0 home draw with Slovakia.

[2] This was Gibraltar's first game since being admitted to UEFA[3] He was the first Gibraltarian footballer to score a winning goal at senior international level since joining UEFA, having struck against Malta in June 2014.

[5] His brothers Lee and Ryan have also played with Gibraltar's national side.